ChemInform Abstract: Synthetic Studies on Actinobolin and Bactobolin: Synthesis of N- Desalanyl-N-(2-(trimethylsilyl)ethanesulfonyl) Derivatives from a Common Intermediate and Attempted Removal of the SES Protecting Group.
✍ Scribed by D. E. WARD; Y. GAI; B. F. KALLER
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 40 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Synthetic Studies on Actinobolin and Bactobolin: Synthesis of N-Desalanyl-N-(2-(trimethylsilyl)ethanesulfonyl) Derivatives from a Common Intermediate and Attempted Removal of the SES Protecting Group.
-Two closely related syntheses of the bactobolin derivative (VIII) from (I), previously prepared from D-glucose, are presented. Key step is the stereoselective addition of LiCHCl2 in the presence of CeCl3 to an α-amino ketone, e.g. (II). An efficient route to (XI), from which actinobolin (XIII) is obtained in 85% yield by a known procedure, from (I) involving an unexpected cyclization of (X) is also described. The removal of the SES protecting group from (VIII) fails, thereby preventing the completion of the total synthesis of bactobolin (IX). -(WARD, D.